Same Old Love
by xxdolphingirl17xx
Summary: Elena is trying to start fresh in New York city but her past keeps bringing her back to the starting point. Can Damon a handsome stranger help her find herself? Damon has his own past too. Will they come together? AU
1. Chapter 1: Elena

Chapter 1

"ELENA! PICKUP!" The obnoxious over-weight cook called out from the front.

"GOT IT THANKS!" She yelled back. Elena was currently hiding in the back of the small restaurant. After ten hours of nothing but dealing with rude customers and co-workers who do nothing but gossip she was sick of this shit. She was supposed to have today off. Of course her dick boss would call her in. She had worked the last five days on double shifts and she was tired to say the least.

 _One more hour Elena. You can do this._ She told herself. Her black apron was covered in grease stains and spots. Her hair, which was once in a tight bun had fallen and turned into a pile of hair on top of her head. She had opted to wear black Nikes, even though they weren't dress code, because she thought they would be more comfortable, but now she just wanted to take them off. She was sure she had makeup smudged somewhere on her face because the cook kept looking at her strange.

As she grabbed her tables' food off the counter she saw her manager stick his head out of his office.

"ELENA! I need to see you in my office as soon as you deliver that." He told her quickly.

 _Fuck, the last person he called in there got fired._ Elena could not afford to lose her job right now. Between her little brothers' tuition payments and rent she was barely making it as it was. She loved Jeremy, don't get her wrong. It's just sometimes she wished she could have gone to New York with the rest of her friends after they graduated instead of staying behind to take care of him. After her parents died though, she knew it was her responsibility. She was all the family he had left.

Elena delivered the customers food with a fake smile for a good tip before heading into her boss's office. She knocked twice on the open door to get his attention. He was busy typing away at the computer. Elena had never really like him. He was a tall lanky man who was always making passes at her. She knew he did it to all the waitresses, it's just that he was gross the way he went about it.

"Elena, I have some bad news." His nasally voice started. He looked up shortly to eye Elena's body up and down before smirking and returning his attention to the computer screen.

"Due to budget cuts we're having to let some people-"He wasn't allowed to finish his sentence before Elena cut him off.

"Mr. Fell, I have worked here since I turned seventeen. I'm almost twenty-three! I work harder than anyone in this damn place and you're just going to 'let me go'?" She questioned angrily with air quotes around the last part of her sentence. Logan Fell was the absolute worse boss ever. He called you in on your days off, payed you little to nothing for the time spent, and fired you if you didn't sleep with him. Elena knew exactly what he was about to say when he stood up and walked around the desk to stand in front of her. Before he could even start to make a pass she started again.

"Don't even try that shit with me. I quit." She quickly undid her apron and tossed it at him before storming off. There was no way in hell she was about to let him talk to her like she was some piece of meat. She walked right out the back and turned down the next street to make her way home. She was tired of this good for nothing, small town. Elena was sick of always having to smile and wave to everyone, pretending she was fine. Otherwise some nosy lady would start bugging her. She sighed as she walked into the center of town and sat down on a small park bench. She took her hair out of its halfway bun and let her chocolate waves fall down her back. It was nearing fall so she couldn't sit outside this late too long or else she was start freezing. Elena sat back and looked at the stars until the weight of what happened really set in.

 _Great going Elena._ She thought. _You just lost your job._

She put her elbows on her knees and covered her face with her hands. What was she supposed to do now? No job meant no money, which meant no rent, which in turn meant no place to live and no money for Jer to go to school. Maybe it was time she start fresh anyway. Bonnie and Caroline, her best friends since the age of five had both offered her a place to stay in New York. While they both lived close to each other Caroline had wanted her own apartment to share with her boyfriend, Tyler. She had moved out of Bonnies place about three months ago. Which meant that Bonnie didn't have a roommate anymore. Perhaps it was meant to be.

Elena looked down at her phone it was nearing ten o'clock. She knew her friends definitely wouldn't be sleeping, but out partying, so she went ahead and called Bonnie. It rang twice before a loud voice answered.

"Elena?!" Caroline screamed.

"Yeah it's me." Elena replied. She could tell Bonnie was out with Caroline because she could hear her telling Caroline to give her the phone.

"Elena are you okay?" Bonnie asked worried. Elena smiled. Bonnie had always been the kind one in the trio. Caroline the obnoxious no filter friend, Elena the compassionate one, and Bonnie the kind down to earth friend.

"I'm fine Bonnie. I had a question I wanted to ask you actually." Elena said hesitantly. She knew her friends had wanted her to come stay with them, but it was still awkward asking after she had just lost her job.

"Before you even ask, yes you can stay with me. Caroline has had your furniture in storage since we graduated so we'll get the guys to set it up and you just need to get here okay?"

Elena pulled the phone away from here ear when she heard a shriek come from Caroline's mouth on the other end.

"Sorry about that Elena, she's just had a little too much to drink tonight." Bonnie told her.

" _I have not! I've only had maybe three or four. Maybe five, I forgot."_ She heard Caroline argue back.

" _It was seven and leave me alone so I can talk to Elena!"_ Bonnie yelled back. "Elena?"

Elena smiled. She missed her friends. This was definitely the right choice.  
"I'm here. Are you sure it's okay?"

"Are you kidding me? I'm surprised you didn't just show up. You're like a sister to me Elena." Bonnie reminded her. It was true though. Bonnie's mother had died shortly after Elena's parents. As a result she and Elena had become a lot closer. They had spent countless nights comforting each other and finishing tubs and tubs of Ben&Jerry's.

"I know. I'm sorry. It's just been a rough couple of years. But it's time for a fresh start, especially away from this town." Elena said confidently. "New job, new city, new me."

"I'm glad to hear it. When do you think you'll make it up here? I have an old friend who might be able to get you a job at a well-known bar. He's super laid back and I'm sure he'll hire you on the spot." Bonnie knew Elena would need a job and her friend paid very well.

"I could probably make it to your place by afternoon tomorrow if I left soon. I just need to pack my bag. That sounds amazing by the way. Think you could give him my number?" Elena asked excitedly.

"I'll do better. I'll have you an interview for tomorrow at seven okay? Send me a text when you're on your way."

"Will do. Thank you Bonnie."

"Anytime 'Lena. Love you."

At that she hung up. She stood up and made the short walk back to her house. She knew it wouldn't take her long to pack so she called Ms. Forbes, the town sheriff and Caroline's mom who was more than willing to look over the house while Elena was gone. Elena smiled when she thought about all the family she had gained when her parents had passed. It made the hurt not cut so deep.

After grabbing two large suitcases and a duffle bag Elena was ready to pack. She made sure to pack any clothes she might need and anything with extreme value. It wasn't much, but she knew she could get anything else she needed while in New York. With her bags packed and her dad's SUV loaded Elena headed to New York.

Little did she know that her entire life was about to change.


	2. Chapter 2: Damon

Chapter 2

Sunlight peered through the window, threatening to scorch anything in its path. It wasn't hot outside, no. But he had been stuck under the covers for the better part of the morning and it was now almost noon. But that's what happens when you spend all night drinking the house supply of bourbon. Maybe the neighbors supply too. He could already feel the splitting headache start from the center of his head spreading like wild fire.

"DAMON. You have to get up!" The annoying yet worried voice rang. Damon didn't remember specifically why he had to get up. Something important, probably. But still he couldn't gather enough energy to get out of his oversized bed.

"Nobody's home Stef. Come back later." Damon grumbled. He cursed when he suddenly felt the need to puke the contents of his stomach. He squeezed his eyes shut and although it passed he was still not up for getting out of his bed.

"Damon enough of this shit." Stefan told him angrily. "I asked for you to be there on time. You promised me Damon."

 _Fuck._ Damon cursed himself as he suddenly remembered.

"I'm sorry Stef." He mumbled sitting up slowly to keep the room from spinning.

Stefan looked at him like he was crazy.

"You're sorry? You do realize that the board wants you out right? That means you'll lose this luxurious lifestyle you're hell-bent on destroying." Stefan told him, crossing his arms over his chest.

Damon loved Stefan, he really did. But his hero hair was just a little too much today. He was standing there are righteous looking in his grey Armani suit. From the top of his annoying hair to his way too expensive Italian shoes he radiated 'saint'. That's what bugged Damon. Stefan wasn't perfect either, he used to get wasted. What gave him the right to come in here acting all bossy and shit? Sure Damon was being a little childish, but hey! He had to have been having the world's worst hangover right about now. Wasn't he allowed a little freedom?

"Do you have anything to say for yourself?" Stefan continued looking at Damon like he was a small child getting reprimanded for stealing a cookie.

Damon stood up closing his eyes for a brief second to fight back the nausea before he began searching for his shirt. He knew it had to be around here somewhere. He mockingly walked past Stefan with his finger on his chin, pretending to be thinking hard.

"Now I knew I had it when I came in here…" Damon spoke. He stood at the front of the bedroom door before clapping his hands once. "Ah there it is!"

He walked over to the other side of the bed a picked up his black dress shirt as Stefan let out a puff of air.

"I'm serious Damon. You have to start making the board meetings. You haven't been to one in two months." His brother reminded him.

"Do you ever get tired of being 'Saint Stefan'? I mean really! It has to be exhausting." Damon teased him.

"Enough Damon!" Stefan huffed. He was tired of dealing with his brothers shit.

"Only kidding little brother. First of all it's been one month. Secondly the board can't throw me out. I own their boring asses, I pay their damn checks. I also know that you, being the loving brother you were, rescheduled for this afternoon. Am I right? No don't tell me. The look on your face gives it away. What time?" He asked with a smug smirk on his face.

"You have an hour to get ready and you better be there Damon. Don't screw it up." Stefan warned him. He started to make his exit before he turned around and spoke. "And Damon?"

"What?"

"I really am a Saint. I have to be to save your sorry ass." Stefan ducked as an empty water bottle when flying past his head. "See you in an hour ass."

"Whatever you say dick."

Damon waited until he heard the front door close before he walked into his oversized bathroom to get ready. He turned on the hot water before jumping in the shower.

Damon knew he had to get his act together. He couldn't keep bowing off his responsibilities as CEO of Salvatore & Sons. It was a stupid name really. His father never shared anything with his sons until he promptly died of heart failure five years ago. At the ripe age of twenty-one Damon became CEO with Stefan as his sidekick. He wasn't even sure what Stefan did. Surely he had some title, right?

Either way he still hated the company name. It reminded him of his father, Giuseppe, who was an all-round class dick. He left about the same time Stefan was born after months and months of cheating on their mother Lilly. After he left Lilly took her sons to Italy to live with her family before she died in a horrible accident. Damon was seven and Stefan was only four. They grew up with their grandparents who loved them with everything they had. Everything had been fine until Giuseppe had died and left everything in Damon's name. Why would he have done that? Damon still couldn't figure it out, but it did make him and his brother millionaires. While Stefan finished school in Italy, Damon had moved to New York to take care of things. He continued to send money home to his grandparents even to today. He had promised to return, but he just never found the time. Damon had tried to get them to come visit but Nona, their grandmother, had refused. Saying she didn't want to visit the country that so cruelly took their grandsons. Damon knew she didn't mean that, she was just afraid of flying. He would make it back home soon though. Probably.

Damon finished getting ready before heading to his baby blue '69 Camaro. That car was truly his pride and joy. He wouldn't even let Stefan drive it. He inspected it before climbing in and making his way to the office. It wasn't too long of a drive. He arrived with ten minutes to spare. Damon rolled his eyes when he walked in to find Stefan waiting in his office.

"You're here. I'm surprised." Stefan noted before standing up to let Damon have his desk back. "I like the suit, is it new?" He commented.

Damon laughed. "Flattery will get you everywhere little brother." He joked. "Let's get to that meeting you were so determined I go to shall we?"

Stefan fidgeted and Damon looked at him confused.

"What is it little brother?"

Stefan looked guilty.

"There's something I should tell you first..."

Damon's jaw clenched. "She's here isn't she?"

"How did you know?" Stefan asked surprised.

"You look like a puppy who just got kicked Stef. Where is she?" Damon asked impatiently.

Stefan didn't have to answer as a perfectly manicured hand knocked on the office door.

"I'm right here _Damon_." The shrill voice said.

"Katherine." Damon spat out. He was not in the mood for her crap.

"Excuse me." Stefan interrupted their stare down when his phone rang.

"I'll join you Stef. Nothing I need to be here for. Right Katherine?" Damon mocked cheerfully.

Katherine simply rolled her eyes before stepping in front of Damon as Stefan exited.

"Move." Damon stared down at her with his ice cold blue eyes.

"Oh please Damon. Are you still not over that? It was like forever ago." Katherine eyed him with her brown doe eyes. Damon simply glared.

"Alright I'll take that as a no. Anyways I need a favor."

Damon let out a breath of air. He found it hysterical that Katherine thought he would _ever_ help her with something. In truth he really was over the whole 'I cheated on you" thing. They actually hung out a couple times since then. But what he couldn't stand was the fact that she kept showing up like she owned the place. It was his company after all! Where was security when he needed it?

Just like always Damon waited for Saint Stefan to come swooping in to tell her they would help. But three minutes passed and he was sure that had to be a record for him, he was _secretly_ in love with her. It had to be a record for Katherine too. How was she not saying anything right now? He looked up to find her inspecting her nails.

"What do you need Katherine?" Damon sighed.

"I knew you would come around!"

Damon rolled his eyes so hard he was sure they were going to fall out.

"Any who I need a job." Katherine said confidently.

Damon laughed to the point where tears were coming out of his eyes. He looked up to find glaring brown eyes.

"Oh you're serious? What happen to your modeling career?" Damon questioned her.

Katherine pursed her lips.

"For some reason people don't see my amazing talent." Katherine complained. "Can't you just let me work at your bar?"

"Katherine you hated working there. Besides you remember the time you sprayed a valued customer with the tap?" Damon reminded her with raised eyebrows.

"Valued? Please. You know he was a dick with no money. Besides I didn't exactly _hate_ it. Please Damon? Pretty please?" Katherine begged with her hands clasped together in front of her. Damon huffed. He just couldn't get rid of this woman.

"I guess you could. But you'll have to train the new girl. Stefan said something about her starting yesterday." Damon told her. "Don't corrupt her okay?" He laughed lightly. In truth he hadn't had the chance to meet this new girl. Bonnie his annoying best friend had demanded he give her a job. Bonnie and Damon had been friends since he got to New York and tried to hook up with her. She clearly wasn't interested in him but he continued just to irritate her. After a couple months they had become best friends. So he couldn't exactly say no to her.

"Thank you Damon! Totally. What's her name?" Katherine asked him excitedly.

"Elena something I think. Stefan hired her yesterday."

"Alright well Miss Elena will be your best waitress in no time!" Katherine told him clapping her hands. Damon laughed before following her out of his office. He stopped when Katherine turned around quickly.

"Damon?" She said quietly.

"Yes Katherine?" Damon replied annoyed.

"Thank you." She said before walking off.

Damon smiled. Katherine could be a real bitch sometimes but when she wanted to she really could be nice. Well almost nice.

 **Hey y'all! I know I totally shouldn't be starting a new story. I'm working on the others I just don't know where to pick up it up at. I hope y'all like this one. I think it might be better than the others haha. Damon and Elena will meet soon! Next chapter soon! If y'all like it don't forget to hit that little button below and leave a review! I would really appreciate it! I'll try to have the third chapter up in the next couple days. Love y'all!**


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